MedKoo Cat#: 412254 | Name: Psycholeine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Psycholeine is isolated from the tropical plant Psychotria oleoides; exhibits somatostatin antagonistic activity on growth hormone secretion.

Chemical Structure

Psycholeine
Psycholeine
CAS#144424-79-3

Theoretical Analysis

MedKoo Cat#: 412254

Name: Psycholeine

CAS#: 144424-79-3

Chemical Formula: C44H50N8

Exact Mass: 690.4158

Molecular Weight: 690.94

Elemental Analysis: C, 76.49; H, 7.29; N, 16.22

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Psycholeine
IUPAC/Chemical Name
(5S,11R)-13,16-dimethyl-1,7-bis((3aR,8aR)-1-methyl-2,3,8,8a-tetrahydropyrrolo[2,3-b]indol-3a(1H)-yl)-5,6,11,12-tetrahydro-5,10b:11,4b-bis(epiminoethano)dibenzo[c,h][2,6]naphthyridine
InChi Key
HEDIOFZXUDVGEU-WATQSORBSA-N
InChi Code
InChI=1S/C44H50N8/c1-26-25-45-37-43-21-24-52(4)40(49-35-29(13-9-15-31(35)43)41-19-22-50(2)38(41)46-33-17-7-5-11-27(33)41)44(26,43)32-16-10-14-30(36(32)48-37)42-20-23-51(3)39(42)47-34-18-8-6-12-28(34)42/h5-18,26,37-40,45-49H,19-25H2,1-4H3/t26?,37-,38+,39+,40+,41+,42+,43?,44?/m0/s1
SMILES Code
CC1CN[C@H]2Nc3c(C14[C@@H]5Nc6c(C24CCN5C)cccc6[C@]78CCN([C@H]7Nc9c8cccc9)C)cccc3[C@]%10%11CCN([C@H]%10Nc%12c%11cccc%12)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 690.94 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Lindovska P, Movassaghi M. Concise Synthesis of (-)-Hodgkinsine, (-)-Calycosidine, (-)-Hodgkinsine B, (-)-Quadrigemine C, and (-)-Psycholeine via Convergent and Directed Modular Assembly of Cyclotryptamines. J Am Chem Soc. 2017 Dec 6;139(48):17590-17596. doi: 10.1021/jacs.7b09929. Epub 2017 Nov 20. PMID: 29058431; PMCID: PMC5733798. 2: Juster RP, Sindi S, Marin MF, Perna A, Hashemi A, Pruessner JC, Lupien SJ. A clinical allostatic load index is associated with burnout symptoms and hypocortisolemic profiles in healthy workers. Psychoneuroendocrinology. 2011 Jul;36(6):797-805. doi: 10.1016/j.psyneuen.2010.11.001. Epub 2010 Dec 3. PMID: 21129851. 3: Lebsack AD, Link JT, Overman LE, Stearns BA. Enantioselective total synthesis of quadrigemine C and psycholeine. J Am Chem Soc. 2002 Aug 7;124(31):9008-9. doi: 10.1021/ja0267425. PMID: 12148978. 4: Rasolonjanahary R, Sévenet T, Guéritte Voegelein F, Kordon C. Psycholeine, a natural alkaloid extracted from Psychotria oleoides, acts as a weak antagonist of somatostatin. Eur J Pharmacol. 1995 Oct 4;285(1):19-23. doi: 10.1016/0014-2999(95)00345-l. PMID: 8846807. 5: Guéritte-Voegelein F, Sévenet T, Pusset J, Adeline MT, Gillet B, Beloeil JC, Guénard D, Potier P, Rasolonjanahary R, Kordon C. Alkaloids from Psychotria oleoides with activity on growth hormone release. J Nat Prod. 1992 Jul;55(7):923-30. doi: 10.1021/np50085a012. PMID: 1402957. 6: Sévenet T. Looking for new drugs: what criteria? J Ethnopharmacol. 1991 Apr;32(1-3):83-90. doi: 10.1016/0378-8741(91)90106-n. PMID: 1881171.